WO2011080972A1 - Organic electroluminescent element - Google Patents
Organic electroluminescent element Download PDFInfo
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- WO2011080972A1 WO2011080972A1 PCT/JP2010/070536 JP2010070536W WO2011080972A1 WO 2011080972 A1 WO2011080972 A1 WO 2011080972A1 JP 2010070536 W JP2010070536 W JP 2010070536W WO 2011080972 A1 WO2011080972 A1 WO 2011080972A1
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- POKDIIRQAWLPNT-YPEHOIGNSA-N C/C=C\c1cccc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2cccc(-[n]3c(c(c4ccccc44)c(cc5)[n]4-c4ccccc4)c5c4c3cccc4)c2)c1N=C Chemical compound C/C=C\c1cccc(-[n](c2ccccc2c2ccc3c4c5cccc4)c2c3[n]5-c2cccc(-[n]3c(c(c4ccccc44)c(cc5)[n]4-c4ccccc4)c5c4c3cccc4)c2)c1N=C POKDIIRQAWLPNT-YPEHOIGNSA-N 0.000 description 1
- GTJPJGVPTUXBBI-UHFFFAOYSA-N CC1=[O]COC(C)=C1 Chemical compound CC1=[O]COC(C)=C1 GTJPJGVPTUXBBI-UHFFFAOYSA-N 0.000 description 1
- SWDNSDCJGGCGPG-UHFFFAOYSA-N Cc1cc(F)cc(F)c1-c1ccccn1 Chemical compound Cc1cc(F)cc(F)c1-c1ccccn1 SWDNSDCJGGCGPG-UHFFFAOYSA-N 0.000 description 1
- UOIWECJBEBHDOD-UHFFFAOYSA-N c(cc1)cc(c(cc2)c3c(c4ccccc44)c2[n]4-c2cccc4c2cccc4)c1[n]3-c1cccc(-[n](c(cccc2)c2c2ccc3c4ccccc44)c2c3[n]4-c2c(cccc3)c3ccc2)c1 Chemical compound c(cc1)cc(c(cc2)c3c(c4ccccc44)c2[n]4-c2cccc4c2cccc4)c1[n]3-c1cccc(-[n](c(cccc2)c2c2ccc3c4ccccc44)c2c3[n]4-c2c(cccc3)c3ccc2)c1 UOIWECJBEBHDOD-UHFFFAOYSA-N 0.000 description 1
- FPSGCSDOIVPQLR-UHFFFAOYSA-N c(cc1)ccc1-[n](c(cccc1)c1c1ccc2c3c4cccc3)c1c2[n]4-c1cc(-[n]2c(c(c3ccccc33)c(cc4)[n]3-c3nc(-[n]5c6ccccc6c6c5cccc6)nc(-[n]5c6ccccc6c6c5cccc6)n3)c4c3c2cccc3)ccc1 Chemical compound c(cc1)ccc1-[n](c(cccc1)c1c1ccc2c3c4cccc3)c1c2[n]4-c1cc(-[n]2c(c(c3ccccc33)c(cc4)[n]3-c3nc(-[n]5c6ccccc6c6c5cccc6)nc(-[n]5c6ccccc6c6c5cccc6)n3)c4c3c2cccc3)ccc1 FPSGCSDOIVPQLR-UHFFFAOYSA-N 0.000 description 1
- DVPSZRFHRFWQNG-UHFFFAOYSA-N c(cc1)ccc1-[n](c1ccccc11)c(cc2)c1c1c2c(cccc2)c2[n]1-c1cccc(-[n](c(cccc2)c2c2ccc3c4ccccc44)c2c3[n]4-c2ccccc2)c1 Chemical compound c(cc1)ccc1-[n](c1ccccc11)c(cc2)c1c1c2c(cccc2)c2[n]1-c1cccc(-[n](c(cccc2)c2c2ccc3c4ccccc44)c2c3[n]4-c2ccccc2)c1 DVPSZRFHRFWQNG-UHFFFAOYSA-N 0.000 description 1
- YUFJNXIOCAHQKI-UHFFFAOYSA-N c(cc1)ccc1-[n](c1ccccc11)c(cc2)c1c1c2c2ccccc2[n]1-c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1ccc2c3ccccc33)c1c2[n]3-c1ccccc1 Chemical compound c(cc1)ccc1-[n](c1ccccc11)c(cc2)c1c1c2c2ccccc2[n]1-c(cc1)ccc1-c(cc1)ccc1-[n](c(cccc1)c1c1ccc2c3ccccc33)c1c2[n]3-c1ccccc1 YUFJNXIOCAHQKI-UHFFFAOYSA-N 0.000 description 1
- PFPOEZFHUONZLC-UHFFFAOYSA-N c(cc1)ccc1-[n](c1ccccc1c1ccc2c3c4cccc3)c1c2[n]4-c1cc(-[n]2c(c(c3ccccc33)c(cc4)[n]3-c3cc(-[n]5c6ccccc6c6c5cccc6)cc(-[n]5c(cccc6)c6c6c5cccc6)c3)c4c3c2cccc3)ccc1 Chemical compound c(cc1)ccc1-[n](c1ccccc1c1ccc2c3c4cccc3)c1c2[n]4-c1cc(-[n]2c(c(c3ccccc33)c(cc4)[n]3-c3cc(-[n]5c6ccccc6c6c5cccc6)cc(-[n]5c(cccc6)c6c6c5cccc6)c3)c4c3c2cccc3)ccc1 PFPOEZFHUONZLC-UHFFFAOYSA-N 0.000 description 1
- XQYYYANJPATUFE-UHFFFAOYSA-N c(cc1)ccc1-[n]1c2c(c(cccc3)c3[n]3-c4ccc(cc(cc5)-[n](c(cccc6)c6c6ccc7c8ccccc88)c6c7[n]8-c6ccccc6)c5c4)c3ccc2c2ccccc12 Chemical compound c(cc1)ccc1-[n]1c2c(c(cccc3)c3[n]3-c4ccc(cc(cc5)-[n](c(cccc6)c6c6ccc7c8ccccc88)c6c7[n]8-c6ccccc6)c5c4)c3ccc2c2ccccc12 XQYYYANJPATUFE-UHFFFAOYSA-N 0.000 description 1
- YGCIKRZRPUIEMV-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-[n](c2ccccc22)c(cc3)c2c2c3c3ccccc3[n]2-c2cccc(-[n](c(cccc3)c3c3ccc4c5ccccc55)c3c4[n]5-c3ccccc3)c2)cc(-c2ccccc2)c1 Chemical compound c(cc1)ccc1-c1cc(-[n](c2ccccc22)c(cc3)c2c2c3c3ccccc3[n]2-c2cccc(-[n](c(cccc3)c3c3ccc4c5ccccc55)c3c4[n]5-c3ccccc3)c2)cc(-c2ccccc2)c1 YGCIKRZRPUIEMV-UHFFFAOYSA-N 0.000 description 1
- MCLSOJWMNOCTLZ-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-[n](c2ccccc22)c(cc3)c2c2c3c(cccc3)c3[n]2-c2cccc(-[n](c(cccc3)c3c3ccc4c5ccccc55)c3c4[n]5-c3ccccc3)c2)ccc1 Chemical compound c(cc1)ccc1-c1nc(-[n](c2ccccc22)c(cc3)c2c2c3c(cccc3)c3[n]2-c2cccc(-[n](c(cccc3)c3c3ccc4c5ccccc55)c3c4[n]5-c3ccccc3)c2)ccc1 MCLSOJWMNOCTLZ-UHFFFAOYSA-N 0.000 description 1
- SXVOKHYFJVNEDC-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2ccccc2)nc(-[n](c2c3cccc2)c(cc2)c3c3c2c2ccccc2[n]3-c2cccc(-[n](c(cccc3)c3c3ccc4c5ccccc55)c3c4[n]5-c3ccccc3)c2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2ccccc2)nc(-[n](c2c3cccc2)c(cc2)c3c3c2c2ccccc2[n]3-c2cccc(-[n](c(cccc3)c3c3ccc4c5ccccc55)c3c4[n]5-c3ccccc3)c2)n1 SXVOKHYFJVNEDC-UHFFFAOYSA-N 0.000 description 1
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Definitions
- the present invention relates to an organic electroluminescent device containing an indolocarbazole compound, and more particularly to a thin film device that emits light by applying an electric field to a light emitting layer made of an organic compound.
- an organic electroluminescence element (hereinafter referred to as an organic EL element) has a light emitting layer and a pair of counter electrodes sandwiching the layer as its simplest structure. That is, in an organic EL element, when an electric field is applied between both electrodes, electrons are injected from the cathode, holes are injected from the anode, and these are recombined in the light emitting layer to emit light. .
- CBP 4,4′-bis (9-carbazolyl) biphenyl
- Ir (ppy) 3 a green phosphorescent material typified by tris (2-phenylpyridine) iridium complex
- CBP has a characteristic that it is easy to flow holes and electrons. The charge injection balance is lost, and excess holes flow out to the electron transport layer side. As a result, the light emission efficiency from Ir (ppy) 3 decreases.
- a host material having high triplet excitation energy and balanced in both charge (hole / electron) injection and transport characteristics is required. Further, a compound that is electrochemically stable and has high heat resistance and excellent amorphous stability is desired, and further improvement is required.
- Patent Document 3 an indolocarbazole compound as shown below is disclosed as a hole transport material.
- Patent Document 4 an indolocarbazole compound as shown below is disclosed as a hole transport material.
- Patent Document 5 discloses an indolocarbazole compound as shown below as a host material, and discloses that an organic EL device using the compound improves luminous efficiency and has high driving stability.
- An object of this invention is to provide the practically useful organic EL element which has high efficiency and high drive stability in view of the said present condition, and a compound suitable for it.
- the present invention relates to an organic electroluminescence device in which an anode, an organic layer including a phosphorescent light emitting layer and a cathode are laminated on a substrate, and a group consisting of a phosphorescent light emitting layer, a hole transport layer, an electron transport layer and a hole blocking layer.
- An organic electroluminescent element comprising an indolocarbazole compound represented by the general formula (1) in at least one organic layer selected from:
- L represents an (m + n + p + q) -valent aromatic hydrocarbon group having 6 to 50 carbon atoms or an (m + n + p + q) -valent aromatic heterocyclic group having 3 to 50 carbon atoms, Y 1 to Y
- Each 4 is represented by any one of formulas (1a-1) to (1a-6), and at least one is a different group.
- m is an integer of 1 to 3
- n is an integer of 1 to 3
- p is an integer of 0 to 3
- q is an integer of 0 to 3
- m + n + p + q is 2 to 6.
- A is independently an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 11 carbon atoms, an aromatic hydrocarbon group having 6 to 50 carbon atoms, or carbon.
- An aromatic heterocyclic group having a number of 3 to 50 is shown.
- R 1 to R 3 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 11 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic group having 3 to 11 carbon atoms. Represents a heterocyclic group.
- R 3 may form a condensed ring together with the six-membered ring which R 3 is attached.
- indolocarbazole compounds represented by general formula (1) indolocarbazole compounds represented by the following general formulas (2) to (7) are more preferred compounds.
- L, A, R 1 to R 3 , m and n are the same as the general formula (1) and the formulas (1a-1) to (1a-6).
- m and n are more preferably 1.
- the organic electroluminescent element preferably has a light emitting layer containing the indolocarbazole compound and a phosphorescent dopant.
- the indolocarbazole compound used in the organic electroluminescence device of the present invention is an indolocarbazole compound represented by the general formula (1).
- L is an aromatic hydrocarbon group having 6 to 50 carbon atoms or an aromatic heterocyclic group having 3 to 50 carbon atoms, and is an (m + n + p + q) valent group.
- Y 1 to Y 4 are groups represented by any of the different formulas (1a-1) to (1a-6).
- m is an integer of 1 to 3
- n is an integer of 1 to 3
- p is an integer of 0 to 3
- q is an integer of 0 to 3
- m + n + p + q is 2 to 6.
- Y 1 to Y 4 are monovalent groups in which R 1 to R 3 and A are substituted on the indolocarbazole skeleton, and a linking group bonded to L is generated from the N atom in the indolocarbazole skeleton.
- the indolocarbazole skeleton is formed by condensing five rings, but there are isomers having different condensation positions.
- Y 1 to Y 4 are groups represented by the formulas (1a-1) to (1a-6), and Y 1 to Y 4 are different groups. At least two of Y 1 to Y 4 are present as different groups.
- L represents an aromatic hydrocarbon group having 6 to 50 carbon atoms and an aromatic heterocyclic group having 3 to 50 carbon atoms.
- L include benzene, naphthalene, fluorene, anthracene, phenanthrene, fluoranthene, pyrene, chrysene, pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, naphthyridine, carbazole, acridine, or an aromatic group in which a plurality of these aromatic rings are connected.
- benzene, pyridine, pyrimidine, triazine, naphthalene, carbazole, or an (m + n + p + q) -valent group generated by removing hydrogen from an aromatic compound in which a plurality of these aromatic rings are connected is used.
- a plurality of the aromatic rings are connected, they may be the same or different.
- the group generated by removing hydrogen from the aromatic compound in which a plurality of aromatic rings are connected include, for example, biphenyl, terphenyl, bipyridine, bipyrimidine, vitriazine, bistriazylbenzene, binaphthalene, phenylpyridine, diphenylpyridine, diphenylpyrimidine , Diphenyltriazine, phenylcarbazole, pyridylcarbazole and the like (m + n + p + q) -valent groups are included, and the connecting position of Y 1 , Y 2 , Y 3 and Y 4 is not limited, and even in the terminal ring, the central part
- the ring may be
- the aromatic hydrocarbon group or aromatic heterocyclic group may have a substituent, and when it has a substituent, preferred substituents include an alkyl group having 1 to 4 carbon atoms and a group having 3 to 6 carbon atoms.
- a group generated from an aromatic compound in which a plurality of aromatic rings are linked is a divalent group, for example, represented by the following formulas (11) to (13).
- Ar 1 to Ar 6 each represents an unsubstituted monocyclic or condensed aromatic ring.
- the total number of substituents is 1 to 10. Preferably it is 1-6, more preferably 1-4. Further, when L, A and R 1 to R 3 have two or more substituents, they may be the same or different. In addition, in the calculation of the carbon number of L, A and R 1 to R 3 , when it has a substituent, the carbon number of the substituent is included.
- Y 1 to Y 4 are represented by the formulas (1a-1) to (1a-6), respectively.
- R 1 , R 2 and R 3 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 11 carbon atoms, Represents a 6-12 aromatic hydrocarbon group or a C3-C11 aromatic heterocyclic group.
- Preferred are hydrogen, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group, a naphthyl group, a carbazolyl group, a quinolyl group, and an isoquinolyl group.
- they are hydrogen, a phenyl group, or a carbazolyl group.
- R 3 forms a condensed ring with the central six-membered ring forming the indolocarbazole skeleton. May be.
- R 3 may be a condensed ring.
- an indole ring is preferable, and in this case, diindolocarbazole is formed. At this time, the indole ring may have a substituent.
- the ring obtained by removing the six-membered ring from the condensed ring formed by condensation includes a pyrrole ring, a furan ring, a thiophene ring, an indole ring, a benzofuran ring, It can be a thiophene ring, a benzene ring, a naphthalene ring or the like. These rings may have a substituent, and are preferably indole rings which may have a substituent. In this case, when the 6-membered ring is included, a carbazole ring may be formed. If R 3 is condensed with the six-membered ring is a case where R 3 has a substitutable hydrogen atoms of the adjacent position is substituted position on the six-membered ring.
- A is independently a monovalent alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 11 carbon atoms, an aromatic hydrocarbon group having 6 to 50 carbon atoms, or an aromatic heterocyclic group having 3 to 50 carbon atoms. Show. Specific examples of preferred A include benzene, naphthalene, fluorene, anthracene, phenanthrene, fluoranthene, pyrene, chrysene, pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, naphthyridine, carbazole, acridine, or aromatics in which a plurality of these are linked.
- a monovalent group generated by removing hydrogen from a compound can be mentioned. More preferably, a monovalent group produced by removing hydrogen from benzene, pyridine, pyrimidine, triazine, naphthalene, carbazole or an aromatic compound in which a plurality of these are linked is used. When a plurality of the aromatic compounds are connected, they may be the same or different.
- Specific examples of the group generated by removing hydrogen from the above-described aromatic compounds linked together include, for example, biphenyl, terphenyl, bipyridine, bipyrimidine, bitriazine, bistriazylbenzene, phenylpyridine, diphenylpyridine, diphenylpyrimidine, diphenyltriazine, phenyl And monovalent groups derived from carbazole, pyridylcarbazole and the like.
- the alkyl group, cycloalkyl group, aromatic hydrocarbon group or aromatic heterocyclic group may have a substituent, and when it has a substituent, preferred substituents include alkyl groups having 1 to 4 carbon atoms, An alkoxy group having 1 to 2 carbon atoms, an acetyl group, an aryl group having 6 to 18 carbon atoms, and a heteroaryl group having 3 to 17 carbon atoms. More preferred are a phenyl group, a naphthyl group, a carbazolyl group, a quinolyl group, and an isoquinolyl group. Further, the substitution position of A with N in the formulas (1a-1) to (1a-6) is not limited.
- n represents an integer of 1 to 3.
- m is an integer from 1 to 2, and more preferably, m is 1.
- n represents an integer of 1 to 3.
- n is an integer from 1 to 2, more preferably n is 1.
- p represents an integer of 0-3.
- p is an integer from 0 to 2, more preferably, p is 0 or 1.
- q represents an integer of 0-3.
- q is an integer from 0 to 2, and more preferably q is 0 or 1.
- the sum of m, n, p and q is an integer of 2-6. It is preferably 2 to 4, more preferably 2 or 3.
- the indolocarbazole compounds represented by the general formula (1) are preferable compounds.
- Indolocarbazole compounds represented by the general formulas (1) to (7) can be synthesized by selecting a raw material according to the structure of the target compound and using a known method.
- Indolocarbazole compounds that give an indolocarbazole skeleton represented by the formula (1a-2) can be obtained by referring to the synthesis examples shown in Archiv der Pharmazie (Weinheim, Germany) 1987, 320 (3), p280-2. Can be synthesized by the following reaction formula.
- indolocarbazole compounds that give an indolocarbazole skeleton represented by formula (1a-3) and formula (1a-4) are The Journal of Organic Chemistry, 2007,72 (15) 5886 and Tetrahedron, 1999, It can be synthesized by the following reaction formula with reference to the synthesis example shown in p.
- indolocarbazole compound represented by the general formula (1) Specific examples of the indolocarbazole compound represented by the general formula (1) are shown below, but the indolocarbazole compound used in the organic electroluminescence device of the present invention is not limited thereto.
- the indolocarbazole compound represented by the general formula (1) is excellent by being contained in at least one organic layer of an organic EL device in which an anode, a plurality of organic layers and a cathode are laminated on a substrate.
- An organic electroluminescent device is provided.
- a light emitting layer, a hole transport layer, an electron transport layer or a hole blocking layer is suitable. More preferably, it may be contained as a host material of a light emitting layer containing a phosphorescent dopant.
- the organic EL device of the present invention has an organic layer having at least one light emitting layer between an anode and a cathode laminated on a substrate, and at least one organic layer contains the indolocarbazole compound.
- the indolocarbazole compound is included in the light emitting layer together with a phosphorescent dopant.
- the structure of the organic EL element of the present invention will be described with reference to the drawings.
- the structure of the organic EL element of the present invention is not limited to the illustrated one.
- FIG. 1 is a cross-sectional view showing a structural example of a general organic EL device used in the present invention, wherein 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, and 5 is a light emitting layer. , 6 represents an electron transport layer, and 7 represents a cathode.
- the organic EL device of the present invention may have an exciton blocking layer adjacent to the light emitting layer, and may have an electron blocking layer between the light emitting layer and the hole injection layer.
- the exciton blocking layer can be inserted on either the anode side or the cathode side of the light emitting layer, or both can be inserted simultaneously.
- the organic EL device of the present invention has a substrate, an anode, a light emitting layer and a cathode as essential layers, but it is preferable to have a hole injecting and transporting layer and an electron injecting and transporting layer in layers other than the essential layers, and further emit light. It is preferable to have a hole blocking layer between the layer and the electron injecting and transporting layer.
- the hole injection / transport layer means either or both of a hole injection layer and a hole transport layer
- the electron injection / transport layer means either or both of an electron injection layer and an electron transport layer.
- the organic EL element of the present invention is preferably supported on a substrate.
- the substrate is not particularly limited as long as it is conventionally used for an organic EL element.
- a substrate made of glass, transparent plastic, quartz, or the like can be used.
- an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
- electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 and ZnO.
- conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 and ZnO.
- an amorphous material such as IDIXO (In 2 O 3 —ZnO) that can form a transparent conductive film may be used.
- these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when the pattern accuracy is not required (about 100 ⁇ m or more) ), A pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. Or when using the substance which can be apply
- the cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
- an electron injecting metal a material having a low work function (4 eV or less) metal
- an alloy a material having a low work function (4 eV or less) metal
- an alloy a material having a low work function (4 eV or less) metal
- an alloy referred to as an electron injecting metal
- an alloy referred to as an electron injecting metal
- a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture
- Suitable are a magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al 2 O 3 ) mixture, a lithium / aluminum mixture, aluminum and the like.
- the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
- the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
- the light emission luminance is improved, which is convenient.
- a transparent or semi-transparent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode after producing the metal with a thickness of 1 to 20 nm on the cathode.
- an element in which both the anode and the cathode are transmissive can be manufactured.
- the light emitting layer is a phosphorescent light emitting layer and includes a phosphorescent dopant and a host material.
- the phosphorescent dopant material preferably contains an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold. Such organometallic complexes are known in the prior art documents and the like, and these can be selected and used.
- Preferable phosphorescent dopants include complexes such as Ir (ppy) 3 having a noble metal element such as Ir as a central metal, complexes such as (Bt) 2 Iracac, and complexes such as (Btp) Ptacac. Specific examples of these complexes are shown below, but are not limited to the following compounds.
- the amount of the phosphorescent dopant contained in the light emitting layer is preferably in the range of 5 to 30% by weight.
- the host material in the light emitting layer it is preferable to use an indolocarbazole compound represented by the general formula (1).
- the material used for the light emitting layer may be a host material other than the indolocarbazole compound.
- An indolocarbazole compound and another host material may be used in combination.
- a plurality of known host materials may be used in combination.
- a known host compound that can be used is preferably a compound that has a hole transporting ability and an electron transporting ability, prevents a long wavelength of light emission, and has a high glass transition temperature.
- host materials are known from a large number of patent documents and can be selected from them.
- Specific examples of the host material are not particularly limited, but include indole derivatives, carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine.
- arylamine derivatives amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, porphyrin compounds, anthraquino Heterocyclic tetracarboxylic acid anhydrides such as dimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene,
- metal complexes typified by metal complexes of Russianine derivatives, 8-quinolinol derivatives, metal phthalocyanines, metal complexes of benzoxazole and benzothiazole derivatives, polysilane compounds, poly (N-vinylcarbazole) derivatives, aniline copolymers, Examples thereof include polymer compounds such
- the injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the luminance of light emission.
- the injection layer can be provided as necessary.
- the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
- the indolocarbazole compound represented by the general formula (1) for the hole blocking layer.
- a known hole blocking layer is used. Materials may be used.
- a hole-blocking layer material the material of the electron carrying layer mentioned later can be used as needed.
- the electron blocking layer is made of a material that has a function of transporting holes and has a very small ability to transport electrons.
- the electron blocking layer blocks the electrons while transporting holes, and the probability of recombination of electrons and holes. Can be improved.
- the indolocarbazole compound represented by the general formula (1) according to the present invention can be used.
- the material for the hole transport layer described later is used as necessary. It can also be used.
- the thickness of the electron blocking layer is preferably 3 to 100 nm, more preferably 5 to 30 nm.
- the exciton blocking layer is a layer for preventing excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer. It becomes possible to efficiently confine in the light emitting layer, and the light emission efficiency of the device can be improved.
- the exciton blocking layer can be inserted on either the anode side or the cathode side adjacent to the light emitting layer, or both can be inserted simultaneously.
- an indolocarbazole compound represented by the general formula (1) can be used as the material for the exciton blocking layer.
- other materials for example, 1,3-dicarbazolylbenzene (mCP), Bis (2-methyl-8-quinolinolato) -4-phenylphenolato aluminum (III) (BAlq).
- the hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.
- the hole transport material has either hole injection or transport or electron barrier properties, and may be either organic or inorganic. Although it is preferable to use the indolocarbazole compound represented by General formula (1) for a positive hole transport layer, arbitrary things can be selected and used from a conventionally well-known compound.
- Examples of known hole transport materials that can be used include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, Examples include styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers. Porphyrin compounds, aromatic tertiary amine compounds, and styryl. It is preferable to use an amine compound, and it is more preferable to use an aromatic tertiary amine compound.
- the electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer can be provided as a single layer or a plurality of layers.
- an electron transport material (which may also serve as a hole blocking material), it is sufficient if it has a function of transmitting electrons injected from the cathode to the light emitting layer.
- any one of conventionally known compounds can be selected and used. For example, nitro-substituted fluorene Derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like.
- a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.
- a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
- Concentrated hydrochloric acid 112.0 g (1.10 mol) was added dropwise over 21 hours to 211.7 g (2.16 mol) of concentrated sulfuric acid while stirring a solution of indium 20.0 g (0.17 mol) in 300 ml of dehydrated diethyl ether at room temperature in a nitrogen atmosphere. Injected hydrogen chloride gas. After stirring the reaction solution at room temperature for 15 hours, 121.0 g of ethyl acetate and 303.2 g of saturated aqueous sodium hydrogen carbonate solution were added.
- the reaction solution was divided into an organic layer and an aqueous layer, and the organic layer was washed with distilled water (2 ⁇ 300 ml) and further washed once with a saturated saline solution, and then the organic layer was dehydrated with magnesium sulfate. After filtering off magnesium sulfate, the solvent was distilled off under reduced pressure. To the obtained viscous liquid, 1000 g of n-hexane was added, and the mixture was heated and stirred. Thereafter, hot filtration was performed to remove insoluble matters. The filtrate was cooled, and the precipitated needle crystals were collected by filtration and dried to obtain Intermediate D 73.3 g (0.32 mol, yield 75%).
- Example 1 Each thin film was laminated at a vacuum degree of 4.0 ⁇ 10 ⁇ 5 Pa by a vacuum deposition method on a glass substrate on which an anode made of ITO having a thickness of 110 nm was formed.
- copper phthalocyanine (CuPC) was formed to a thickness of 25 nm on ITO.
- NPB 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
- compound 3-15 obtained in Synthesis Example 1 as a host material, tris (2-phenylpyridine) iridium (III) (Ir (ppy) 3 ) as a phosphorescent dopant, and Were co-deposited from different deposition sources to form a light emitting layer with a thickness of 40 nm.
- the concentration of Ir (ppy) 3 in the light emitting layer was 10.0 wt%.
- tris (8-hydroxyquinolinato) aluminum (III) (Alq3) was formed to a thickness of 20 nm as an electron transport layer.
- lithium fluoride (LiF) was formed to a thickness of 1.0 nm as an electron injection layer.
- aluminum (Al) was formed as an electrode to a thickness of 70 nm to produce an organic EL element.
- the organic EL element had the light emission characteristics as shown in Table 1.
- Table 1 the luminance, voltage, and luminous efficiency show values at 10 mA / cm 2 . Further, the luminance half time is evaluated by constant current drive of 40 mA / cm 2 , and the result is converted into a value when the initial luminance is 1000 cd / m 2 . The maximum wavelength of the device emission spectrum was 520 nm, and it was found that light emission from Ir (ppy) 3 was obtained.
- Example 2 An organic EL device was produced in the same manner as in Example 1 except that Compound 1-31 was used as the host material for the light emitting layer.
- Example 3 An organic EL device was produced in the same manner as in Example 1 except that Compound 2-3 was used as the host material for the light emitting layer.
- Example 4 An organic EL device was produced in the same manner as in Example 1 except that Compound 3-22 was used as the host material for the light emitting layer.
- Example 5 An organic EL device was produced in the same manner as in Example 1 except that Compound 5-19 was used as the host material for the light emitting layer.
- Example 6 An organic EL device was produced in the same manner as in Example 1 except that Compound 6-11 was used as the host material for the light emitting layer.
- Example 7 An organic EL device was produced in the same manner as in Example 1 except that Compound 6-17 was used as the host material for the light emitting layer.
- Example 8 An organic EL device was produced in the same manner as in Example 1 except that Compound 6-30 was used as the host material for the light emitting layer.
- Comparative Example 1 An organic EL device was produced in the same manner as in Example 1 except that the following compound H-1 was used as the host material for the light emitting layer.
- the organic EL elements of Examples 1 to 8 have improved initial characteristics and lifetime characteristics as compared with Comparative Example 1. From this, a material having a different indolocarbazole skeleton in one molecule is used as a main component of the light emitting layer. This shows that the characteristics of the organic EL element are improved.
- the indolocarbazole compound used in the organic electroluminescence device of the present invention has two or more types of indolocarbazole isomer skeleton in one molecule, or a bond having an asymmetric molecular structure even in the same isomer.
- By having a mode it becomes possible to finely adjust the hole and electron transfer speeds and to control various energy values of IP, EA, and T1.
- the optimum carrier balance in the light emitting layer is realized, and the effect characteristics can be greatly improved.
- this indolocarbazole compound can improve stability in each active state of oxidation, reduction, and excitation, and at the same time has good amorphous characteristics, so it has a long driving life and high durability. An element can be realized.
- a material design provided with functions such as improvement in solubility is possible, and a material more suitable for a wet process can be provided.
- the organic EL device according to the present invention has practically satisfactory levels in terms of light emission characteristics, driving life and durability, flat panel display (mobile phone display device, in-vehicle display device, OA computer display device, television, etc.), surface light emission, etc. Its technical value is great in applications to light sources (lighting, light sources for copying machines, backlight light sources for liquid crystal displays and instruments), display boards, and sign lamps that make use of the characteristics of the body.
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Abstract
Description
In
Patent Document 5 discloses an indolocarbazole compound as shown below as a host material, and discloses that an organic EL device using the compound improves luminous efficiency and has high driving stability.
In the general formula (1), L represents an (m + n + p + q) -valent aromatic hydrocarbon group having 6 to 50 carbon atoms or an (m + n + p + q) -valent aromatic heterocyclic group having 3 to 50 carbon atoms, Y 1 to Y Each 4 is represented by any one of formulas (1a-1) to (1a-6), and at least one is a different group. m is an integer of 1 to 3, n is an integer of 1 to 3, p is an integer of 0 to 3, q is an integer of 0 to 3, and m + n + p + q is 2 to 6.
(式(11)~(13)中、Ar1~Ar6は無置換の単環又は縮合環の芳香環を表す。)
(In the formulas (11) to (13), Ar 1 to Ar 6 each represents an unsubstituted monocyclic or condensed aromatic ring.)
本発明の有機EL素子は、基板に支持されていることが好ましい。この基板については、特に制限はなく、従来から有機EL素子に慣用されているものであればよく、例えば、ガラス、透明プラスチック、石英などからなるものを用いることができる。 -substrate-
The organic EL element of the present invention is preferably supported on a substrate. The substrate is not particularly limited as long as it is conventionally used for an organic EL element. For example, a substrate made of glass, transparent plastic, quartz, or the like can be used.
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としてはAu等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。また、IDIXO(In2O3-ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極はこれらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、あるいはパターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。あるいは、有機導電性化合物のように塗布可能な物質を用いる場合には、印刷方式、コーティング方式等湿式成膜法を用いることもできる。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。更に膜厚は材料にもよるが、通常10~1000nm、好ましくは10~200nmの範囲で選ばれる。 -anode-
As the anode in the organic EL element, an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used. Specific examples of such electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 and ZnO. Alternatively, an amorphous material such as IDIXO (In 2 O 3 —ZnO) that can form a transparent conductive film may be used. For the anode, these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when the pattern accuracy is not required (about 100 μm or more) ), A pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. Or when using the substance which can be apply | coated like an organic electroconductivity compound, wet film-forming methods, such as a printing system and a coating system, can also be used. When light emission is extracted from the anode, it is desirable that the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred Ω / □ or less. Further, although the film thickness depends on the material, it is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.
一方、陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム-カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着やスパッタリング等の方法により薄膜を形成させることにより、作製することができる。また、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm~5μm、好ましくは50~200nmの範囲で選ばれる。なお、発光した光を透過させるため、有機EL素子の陽極又は陰極のいずれか一方が、透明又は半透明であれば発光輝度が向上し好都合である。 -cathode-
On the other hand, as the cathode, a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used. Specific examples of such electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like. Among these, from the point of durability against electron injection and oxidation, etc., a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this, for example, a magnesium / silver mixture, Suitable are a magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al 2 O 3 ) mixture, a lithium / aluminum mixture, aluminum and the like. The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually selected in the range of 10 nm to 5 μm, preferably 50 to 200 nm. In order to transmit the emitted light, if either one of the anode or the cathode of the organic EL element is transparent or translucent, the light emission luminance is improved, which is convenient.
発光層は燐光発光層であり、燐光発光ドーパントとホスト材料を含む。燐光発光ドーパント材料としては、ルテニウム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金から選ばれる少なくとも一つの金属を含む有機金属錯体を含有するものがよい。かかる有機金属錯体は、前記先行技術文献等で公知であり、これらが選択されて使用可能である。 -Light emitting layer-
The light emitting layer is a phosphorescent light emitting layer and includes a phosphorescent dopant and a host material. The phosphorescent dopant material preferably contains an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold. Such organometallic complexes are known in the prior art documents and the like, and these can be selected and used.
注入層とは、駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる層のことで、正孔注入層と電子注入層があり、陽極と発光層又は正孔輸送層の間、及び陰極と発光層又は電子輸送層との間に存在させてもよい。注入層は必要に応じて設けることができる。 -Injection layer-
The injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the luminance of light emission. There are a hole injection layer and an electron injection layer, and between the anode and the light emitting layer or the hole transport layer. And between the cathode and the light emitting layer or the electron transport layer. The injection layer can be provided as necessary.
正孔阻止層とは広い意味では電子輸送層の機能を有し、電子を輸送する機能を有しつつ正孔を輸送する能力が著しく小さい正孔阻止材料からなり、電子を輸送しつつ正孔を阻止することで電子と正孔の再結合確率を向上させることができる。 -Hole blocking layer-
The hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking.
電子阻止層とは、正孔を輸送する機能を有しつつ電子を輸送する能力が著しく小さい材料から成り、正孔を輸送しつつ電子を阻止することで電子と正孔が再結合する確率を向上させることができる。 -Electron blocking layer-
The electron blocking layer is made of a material that has a function of transporting holes and has a very small ability to transport electrons. The electron blocking layer blocks the electrons while transporting holes, and the probability of recombination of electrons and holes. Can be improved.
励起子阻止層とは、発光層内で正孔と電子が再結合することにより生じた励起子が電荷輸送層に拡散することを阻止するための層であり、本層の挿入により励起子を効率的に発光層内に閉じ込めることが可能となり、素子の発光効率を向上させることができる。励起子阻止層は発光層に隣接して陽極側、陰極側のいずれにも挿入することができ、両方同時に挿入することも可能である。 -Exciton blocking layer-
The exciton blocking layer is a layer for preventing excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer. It becomes possible to efficiently confine in the light emitting layer, and the light emission efficiency of the device can be improved. The exciton blocking layer can be inserted on either the anode side or the cathode side adjacent to the light emitting layer, or both can be inserted simultaneously.
正孔輸送層とは正孔を輸送する機能を有する正孔輸送材料からなり、正孔輸送層は単層又は複数層設けることができる。 -Hole transport layer-
The hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.
電子輸送層とは電子を輸送する機能を有する材料からなり、電子輸送層は単層又は複数層設けることができる。 -Electron transport layer-
The electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer can be provided as a single layer or a plurality of layers.
APCI-TOFMS, m/z 523 [M+H]+ Under a nitrogen atmosphere, 1.6 g of 56% sodium hydride and 50 ml of dehydrated N, N-dimethylformamide were added and stirred. Next, a solution prepared by dissolving 10.0 g (0.030 mol) of Intermediate C in 60 ml of dehydrated N, N-dimethylformamide was added dropwise over 30 minutes. Thereafter, stirring was continued for 1 hour. Next, a solution prepared by dissolving 7.0 g (0.031 mol) of Intermediate D in 60 ml of dehydrated N, N-dimethylformamide was added dropwise over 30 minutes. Thereafter, stirring was continued for a whole day and night. Next, 300 g of distilled water was added to the flask, and the precipitated yellow crystals were collected by filtration. The yellow crystals collected by filtration were reslurried and dried to obtain 15.0 g of Intermediate E (0.029 mol, yield 96%).
APCI-TOFMS, m / z 523 [M + H] +
APCI-TOFMS, m/z 818 [M+H]+、1H -NMR測定結果(測定溶媒:THF-d8)を図2に示す。 Under a nitrogen atmosphere, 2.4 g of 56% sodium hydride and 130 ml of dehydrated N, N-dimethylformamide were added and stirred. Next, a solution prepared by dissolving 15.4 g (0.046 mol) of Intermediate B in 154 ml of dehydrated N, N-dimethylformamide was added dropwise over 30 minutes. Thereafter, stirring was continued for 1 hour. Next, a solution prepared by dissolving 22.0 g (0.042 mol) of the intermediate E in 220 ml of dehydrated N, N-dimethylformamide was added dropwise over 30 minutes. Thereafter, stirring was continued for 4 hours. Next, 500 g of distilled water was added to the flask, and the precipitated yellow crystals were collected by filtration. The yellow crystals collected by filtration were reslurried and dried. Thereafter, purification was performed on a silica gel column to obtain 9.2 g (0.011 mol, yield 27%) of compound 3-15.
APCI-TOFMS, m / z 818 [M + H] + , 1 H -NMR measurement results (measuring solvent: THF-d8) are shown in FIG.
膜厚110 nmのITOからなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度4.0×10-5 Paで積層させた。まず、ITO上に銅フタロシアニン(CuPC)を25 nmの厚さに形成した。次に、正孔輸送層として4,4'-ビス[N-(1-ナフチル)-N-フェニルアミノ]ビフェニル(NPB)を40 nmの厚さに形成した。次に、正孔輸送層上に、ホスト材料としての合成例1で得た化合物3-15と、燐光発光ドーパントとしてのトリス(2‐フェニルピリジン)イリジウム(III)(Ir(ppy)3)とを異なる蒸着源から、共蒸着し、40 nmの厚さに発光層を形成した。発光層中のIr(ppy)3の濃度は10.0 wt%であった。次に、電子輸送層としてトリス(8-ヒドロキシキノリナト)アルミニウム(III)(Alq3)を20 nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を1.0 nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を70 nmの厚さに形成し、有機EL素子を作製した。 Example 1
Each thin film was laminated at a vacuum degree of 4.0 × 10 −5 Pa by a vacuum deposition method on a glass substrate on which an anode made of ITO having a thickness of 110 nm was formed. First, copper phthalocyanine (CuPC) was formed to a thickness of 25 nm on ITO. Next, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) was formed to a thickness of 40 nm as a hole transport layer. Next, on the hole transport layer, compound 3-15 obtained in Synthesis Example 1 as a host material, tris (2-phenylpyridine) iridium (III) (Ir (ppy) 3 ) as a phosphorescent dopant, and Were co-deposited from different deposition sources to form a light emitting layer with a thickness of 40 nm. The concentration of Ir (ppy) 3 in the light emitting layer was 10.0 wt%. Next, tris (8-hydroxyquinolinato) aluminum (III) (Alq3) was formed to a thickness of 20 nm as an electron transport layer. Further, on the electron transport layer, lithium fluoride (LiF) was formed to a thickness of 1.0 nm as an electron injection layer. Finally, on the electron injection layer, aluminum (Al) was formed as an electrode to a thickness of 70 nm to produce an organic EL element.
発光層のホスト材料として、化合物1-31を用いた以外は実施例1と同様にして有機EL素子を作製した。 Example 2
An organic EL device was produced in the same manner as in Example 1 except that Compound 1-31 was used as the host material for the light emitting layer.
発光層のホスト材料として、化合物2-3を用いた以外は実施例1と同様にして有機EL素子を作製した。 Example 3
An organic EL device was produced in the same manner as in Example 1 except that Compound 2-3 was used as the host material for the light emitting layer.
発光層のホスト材料として、化合物3-22を用いた以外は実施例1と同様にして有機EL素子を作製した。 Example 4
An organic EL device was produced in the same manner as in Example 1 except that Compound 3-22 was used as the host material for the light emitting layer.
発光層のホスト材料として、化合物5-19を用いた以外は実施例1と同様にして有機EL素子を作製した。 Example 5
An organic EL device was produced in the same manner as in Example 1 except that Compound 5-19 was used as the host material for the light emitting layer.
発光層のホスト材料として、化合物6-11を用いた以外は実施例1と同様にして有機EL素子を作製した。 Example 6
An organic EL device was produced in the same manner as in Example 1 except that Compound 6-11 was used as the host material for the light emitting layer.
発光層のホスト材料として、化合物6-17を用いた以外は実施例1と同様にして有機EL素子を作製した。 Example 7
An organic EL device was produced in the same manner as in Example 1 except that Compound 6-17 was used as the host material for the light emitting layer.
発光層のホスト材料として、化合物6-30を用いた以外は実施例1と同様にして有機EL素子を作製した。 Example 8
An organic EL device was produced in the same manner as in Example 1 except that Compound 6-30 was used as the host material for the light emitting layer.
発光層のホスト材料として、下記化合物H-1を用いた以外は実施例1と同様にして有機EL素子を作製した。 Comparative Example 1
An organic EL device was produced in the same manner as in Example 1 except that the following compound H-1 was used as the host material for the light emitting layer.
本発明による有機EL素子は、発光特性、駆動寿命ならびに耐久性において、実用上満足できるレベルにあり、フラットパネルディスプレイ(携帯電話表示素子、車載表示素子、OAコンピュータ表示素子やテレビ等)、面発光体としての特徴を生かした光源(照明、複写機の光源、液晶ディスプレイや計器類のバックライト光源)、表示板や標識灯等への応用において、その技術的価値は大きいものである。 The indolocarbazole compound used in the organic electroluminescence device of the present invention has two or more types of indolocarbazole isomer skeleton in one molecule, or a bond having an asymmetric molecular structure even in the same isomer. By having a mode, it becomes possible to finely adjust the hole and electron transfer speeds and to control various energy values of IP, EA, and T1. As a result, in the organic EL device using the indolocarbazole compound, the optimum carrier balance in the light emitting layer is realized, and the effect characteristics can be greatly improved. Furthermore, this indolocarbazole compound can improve stability in each active state of oxidation, reduction, and excitation, and at the same time has good amorphous characteristics, so it has a long driving life and high durability. An element can be realized. In addition, a material design provided with functions such as improvement in solubility is possible, and a material more suitable for a wet process can be provided.
The organic EL device according to the present invention has practically satisfactory levels in terms of light emission characteristics, driving life and durability, flat panel display (mobile phone display device, in-vehicle display device, OA computer display device, television, etc.), surface light emission, etc. Its technical value is great in applications to light sources (lighting, light sources for copying machines, backlight light sources for liquid crystal displays and instruments), display boards, and sign lamps that make use of the characteristics of the body.
Claims (4)
- 基板上に、陽極、燐光発光層を含む有機層及び陰極が積層されてなる有機電界発光素子において、燐光発光層、正孔輸送層、電子輸送層及び正孔阻止層からなる群れから選ばれる少なくとも一つの有機層中に、一般式(1)で表されるインドロカルバゾール化合物を含有することを特徴とする有機電界発光素子。
一般式(1)中、Lは(m+n+p+q)価の炭素数6~50の芳香族炭化水素基又は炭素数3~50の芳香族複素環基を表し、Y1~Y4はそれぞれ式(1a-1)~(1a-6)のいずれかで表される基であり、少なくとも1つは異なる基である。mは1~3の整数、nは1~3の整数、pは0~3の整数、qは0~3の整数を表し、m+n+p+qは2~6である。
式(1a-1)~(1a-6)中、Aは独立に炭素数1~10のアルキル基、炭素数3~11のシクロアルキル基、炭素数6~50の芳香族炭化水素基又は炭素数3~50の芳香族複素環基を示す。R1~R3はそれぞれ独立に、水素、炭素数1~10のアルキル基、炭素数3~11のシクロアルキル基、炭素数6~12の芳香族炭化水素基又は炭素数3~11の芳香族複素環基を示す。ただし、式(1a-1)、(1a-2)、(1a-4)及び(1a-6)において、R3はR3が結合する六員環と共に縮合環を形成しても良い。 In an organic electroluminescent device in which an anode, an organic layer including a phosphorescent light emitting layer and a cathode are laminated on a substrate, at least selected from the group consisting of a phosphorescent light emitting layer, a hole transport layer, an electron transport layer and a hole blocking layer An organic electroluminescent device comprising an indolocarbazole compound represented by the general formula (1) in one organic layer.
In the general formula (1), L represents an (m + n + p + q) -valent aromatic hydrocarbon group having 6 to 50 carbon atoms or an aromatic heterocyclic group having 3 to 50 carbon atoms, and Y 1 to Y 4 are each represented by the formula (1a -1) to (1a-6), and at least one is a different group. m is an integer of 1 to 3, n is an integer of 1 to 3, p is an integer of 0 to 3, q is an integer of 0 to 3, and m + n + p + q is 2 to 6.
In formulas (1a-1) to (1a-6), A is independently an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 11 carbon atoms, an aromatic hydrocarbon group having 6 to 50 carbon atoms, or carbon. An aromatic heterocyclic group having a number of 3 to 50 is shown. R 1 to R 3 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 11 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic group having 3 to 11 carbon atoms. Represents a heterocyclic group. However, the formula (1a-1), (1a -2), in (1a-4) and (1a-6), R 3 may form a condensed ring together with the six-membered ring to which R 3 binds. - 一般式(1)で表されるインドロカルバゾール化合物が、一般式(2)~(7)のいずれかで表されるインドロカルバゾール化合物である請求項1に記載の有機電界発光素子。
一般式(2)~(7)中、L、A、R1~R3、m及びnは一般式(1)及び式(1a-1)~(1a-6)と同意である。 The organic electroluminescent device according to claim 1, wherein the indolocarbazole compound represented by the general formula (1) is an indolocarbazole compound represented by any one of the general formulas (2) to (7).
In the general formulas (2) to (7), L, A, R 1 to R 3 , m and n are the same as the general formula (1) and the formulas (1a-1) to (1a-6). - 一般式(2)~(7)で表されるインドロカルバゾール化合物において、m及びnがそれぞれ1である請求項2に記載の有機電界発光素子。 The organic electroluminescent device according to claim 2, wherein m and n are each 1 in the indolocarbazole compounds represented by the general formulas (2) to (7).
- インドロカルバゾール化合物を含む有機層が、燐光発光ドーパントを含有する発光層であることを特徴とする請求項1~3のいずれかに記載の有機電界発光素子。 4. The organic electroluminescent device according to claim 1, wherein the organic layer containing an indolocarbazole compound is a light emitting layer containing a phosphorescent dopant.
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WO2019181465A1 (en) | 2018-03-19 | 2019-09-26 | 日鉄ケミカル&マテリアル株式会社 | Organic electroluminescence element |
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CN102696126A (en) | 2012-09-26 |
TWI485228B (en) | 2015-05-21 |
CN102696126B (en) | 2015-06-10 |
EP2521196A4 (en) | 2017-12-27 |
EP2521196A1 (en) | 2012-11-07 |
KR20120123368A (en) | 2012-11-08 |
TW201130950A (en) | 2011-09-16 |
EP2521196B1 (en) | 2018-09-12 |
US20120235133A1 (en) | 2012-09-20 |
JP5596706B2 (en) | 2014-09-24 |
US9260433B2 (en) | 2016-02-16 |
JPWO2011080972A1 (en) | 2013-05-09 |
KR101758865B1 (en) | 2017-07-17 |
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